[BUG] Conversation Data Loss (Web Interface)

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Two potentially related issues:

1. Midstream conversation loss
2. Chat history Loss

Midstream Conversation Loss

Me: I'm going to give you three attachments
C: Okay, waiting
Me: Uploads attachment 1
C: Logged, give me the next
Me: Uploads attachment 2
C: Logged, give me the next
Me: Uploads attachment 3
C: Logged, anything else? 
Me: No, start the analysis.
C: You only gave me 1 document, did you mean to give me 3?

At this point, I scroll back up and my conversation looks like this:

Me: I'm going to give you three attachments
C: Okay, waiting
Me: Uploads attachment 1
C: Logged, give me the next
Me: No, start the analysis.
C: You only gave me 1 document, did you mean to give me 3?

This happens frequently

Chat History Loss

Entire chats disappear. I've even seen instances where ALL of my chats disappear. This just happened, and I'm uncertain it will come back.

See: #14225 <- not sure why this was closed, it's a critical unfixed issue.

What Should Happen?

This data should not be lost. Cache it locally and restore if needed, but make sure it doesn't drop entirely. This is reminiscent of the MS Word days before AutoSave, but with an aggressive toddler randomly shutting down the computer. Unacceptable for a production tool.

Error Messages/Logs

Steps to Reproduce

Inconsistent, See description of what I saw above.

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Uncertain, conversation lost!

Platform

Other

Operating System

Windows

Terminal/Shell

Other

Additional Information

_No response_